One Step at A Time
by LordMomo
Summary: After loss after loss, May is eager to put her latest downfall behind her as she visits Alola to take her younger brother Max to Pokemon school. Of course, there she's also planning on meeting a certain raven-haired trainer as well. One-shot. Winner of The Advancers Unofficial Fanfiction Contest 2017!


**A/N: This story was written as a part of the Advanceshipping contest on Advancers. Thank you for everyone who encouraged me to continue to write, especially Wubbzy. Love you all!** **Enjoy!**

* * *

 _ **Alola Harbour.**_

 _ **Sunrise.**_

 _ **7 am**._

The eastern port filled up brilliantly with the light of a new day. Miraculous hues of orange, red, pink, and lavender, danced atop the water in a stunning array of colour that the fourteen year old brunette had never seen before. Just the trip up here, had been worth it.

"Alola… it's amazing." May smiled to herself as she took in a deep breath of the warm island air.

Hoenn – the brunette's home region - was gorgeous in its own right, but Alola had its own charm. The beautiful tropical region, topped with the distinct vibrant culture of the islands, made it unique. Music filled the air as the soft sounds of steel drums were being played in the distance. May's body involuntary started swaying to the music…

Until a certain voice ringed out that snapped her out of her momentary bliss.

"May, hurry up! Stop doing your stupid expeditions and help us unpack!" The younger Maple yelled at his older sister. May groaned internally. _So much for enjoying the view. Why are younger siblings so annoying_?

"I'm coming, I'm coming! Jeez Max, and I thought you were annoying when you were younger…" She shook her head at the ten year old in front of her, who just stuck his tongue out cheekily then adjusted his glasses.

Both of the Maple's had grown up quite a bit since going on their first adventure four years ago, the biggest difference being in their height. Max now stood at five feet tall, taller than normal for a ten year old thanks in part to genetics from his father. He was sporting a white t-shirt along with a forest green button up t-shirt on top, as well as tan-coloured cargo shorts. His hair was a little shorter than it used to be, mainly due to their mother insisting Max keep it out of his eyes. He still had that youthful look on his face - which he hated, as he insisted he was an 'adult'.

May, while also getting a bit taller, let down her hair from her signature two ponytail look that she loved, into a slightly more practical look. She pulled up her brown locks into a high ponytail, as the humidity in the region was starting to get to her. She reached into her pocket and pulled out her handy signature red bandanna and tied it around her head, leaving the knot at the top that formed a small pair of cat-esque ears. She smiled as she looked at her reflection in the taxi window, fixing the bandanna. Her striking sapphire eyes had always been her favourite part about herself, second only to her silky brown hair. May was dressed in a comfy pair of black biker shorts that reached just above her knees, with white short-shorts situated on top of them. She dressed herself in a red and black t-shirt style top, complete with her yellow fanny pack that sit snugly at her waist.

"Which one is your dorm, Max?" May asked her younger brother as she stared the gigantic school building in front of her in awe. It was simply amazing. The sunlight reflected off the seemingly endless panes of glass. The building wasn't shaped like a traditional rectangular-shaped building, rather it was almost an architectural marvel, with bits and pieces of the building sticking out into odd shapes and tunnels.

"That cylinder looking one on the right, that's what Professor Oak said. Didn't you pay attention when he was explaining, May?" The boy shook his head.

"Er-no… That's why I asked, duh." She giggled as she pulled Max's luggage into the correct building, remembering their conversation with the old professor. In reality, May had stopped paying attention once the Pokémon professor had mentioned the words 'Ash is also going to visit Alola'. She was ecstatic to learn all about what Ash was doing in person. It had almost been a year since she last saw him, after all.

The bright lobby looked inviting, buzzing with several students standing around at the front desk, some with adults helping them fill out the forms, presumably the student's parents.

"May, what would you do without me?" Max sighed as he pulled the other luggage into the lobby. As he stabilized his luggage, he looked around at the lobby and then immediately perked up when he saw the other kids signing up.

"Oh boy, Professor Oak was right, this is going to be great!" He said excitedly as he walked over to the front desk amongst other kids almost his age. The mid-aged receptionist looked up at him and raised her eyebrow inquisitively.

"Ah, so you're the Max that Professor Oak recommended to come to our school. You must be quite the young man. It's not often we get a recommendation straight from Professor Oak himself. " The receptionist quipped as she pulled out his paperwork.

Max beamed, while May also couldn't help but smile and be proud of her younger sibling. Professor Oak had personally gotten Max admission to the Alolan school, and as part of May's older sister duty, she had assured her parents she would help Max get settled into the new school. It worked out for everyone in the end, because May scored herself a vacation at the same time. Though, it wasn't really the vacation that had May keen on visiting the tropical region, it was the certain trainer who was also arriving to pick up his school diploma that had her excited.

"May, you're blushing…" Max smirked at his older sister as he finished giving the paperwork back to the receptionist. May immediately started fanning herself with her hands.

"It's really hot, that's why!" May lied between her teeth. I mean, it was warm, but nothing May didn't experience in Hoenn at times. She cursed herself in her head because the last thing she wanted was for Max to tease her. Lord knows he wouldn't stop until she had grey hairs…

She smiled to herself as she tried to imagine all the new stories her best friend would tell her when he arrived. What new Pokemon had he caught? What new friends did he make? Did he change at all? Would he be the same Ash? Or did he actually get more mature this time? She couldn't help but feel giddy with anticipation.

 _He actually kept his promise to me._

* * *

 ** _Kanto._**

 ** _6 pm._**

 ** _Ketchum Residence._**

 ** _One year ago._**

"You never even talk to us anymore."

May frowned and crossed her arms on the comfy couch in Ash's living room. As part of a seasonal tradition, Ash's mother had invited all of Ash's old friends for a small get-together after Ash just completed his journey in the Orre region.

"I'm really, really, REALLY, sorry May, I'm just so busy now… Training is getting harder and harder everyday, sometimes I don't even think I can keep up," Ash said defeated, looking slightly embarrassed. May frowned even more at his answer, not because she was mad that he pulled the _'I'm busy'_ card, but because he actually had a valid reason to be busy. Training would always take precedence over absolutely anything for the boy. She sighed and sunk into the couch more, feeling unquestionably defeated.

"I know Ash, it's okay… I just miss travelling with you." May said admittedly, travelling with rivals would never be the same as travelling with friends, especially with someone as unbelievably supportive as Ash, who always went out of his way to help anyone. May huffed, she was sort of angry at Ash, he set the bar way too high when it came to friends.

"AHEM." Brock coughed loudly, breaking May out of her thoughts.

"You guys too, of course!" May said, immediately flustered. "I mean, who else would cook for me, right?" She grinned at the squinting trainer, who gave her a look.

"Of course, I miss travelling with you too May… All of you." Ash added before getting the same look from Brock, who eased up after hearing the last bit of Ash's sentence.

The others began to talk as Ash tuned out all the conversations around him. He was facing a dilemma, and he had to fix it now.

Starting over every region was taking a toll on the fourteen year old trainer. Not because he was tired of travelling - he lived for travelling. But because he had to leave everything behind.

Ever since he was a little boy, he wanted to be the very best. But did that mean leaving both his friends and Pokémon behind every time he wanted to move onto a new region? He was beginning to question his methods. They evidently weren't giving him any results in the past. He would always come so close to tasting sweet victory each time, but he just didn't cut it.

Ash decided he needed some air, to clear his thoughts.

He rose from his seat after excusing himself and went out to the backyard, leaning against the wooden ledge of the patio. A cool breeze ruffled his black hair. The sound of grass moving in the wind always calmed him down. Pikachu followed him and jumped up to Ash's shoulder, sensing his trainer's inner predicament. The yellow mouse-like Pokémon nuzzled against Ash's cheek.

"Ash, are you alright?"

Ash turned his head in the brunette's direction. The dim light from behind her covered her in a warm glow, her sapphire eyes making contact with his, boring into them as if she could see everything he was thinking. Ash gulped, feeling like a deer in headlights.

"I just have a lot going through my head right now…" He admitted as May also leaned against the ledge of the patio with him. May smiled a bit, knowingly.

"You looked a little spaced out there, what's bothering you?" May inquired. She had known Ash long enough to know that when he got too quiet, he was conflicted about something.

Ash sighed as he looked into her sapphire eyes. They had an understanding warmth about them. They made him feel calm. Possibly because he had taught her since the beginning of her journey and she was almost in the same boat as he was. Making it to the top but never quite able to grasp the victory she deserved, the Ribbon Cup. Ash wanted her to achieve victory just as much as he wanted to reach his goal.

"I was just thinking about all of my journeys up to now. You know, I wouldn't consider myself a failure, not many trainers can make it to the top two, hell, or even top sixteen." He started.

"But there comes a time when you need to think about why you're not able to achieve your ultimate goal. And I think I've figured it out May…"

May raised her eyebrow. She was genuinely hooked onto what Ash was about to say. Ash rarely was the kind to get super serious like he was now, and to see him so conflicted like this was definitely starting to worry her.

"And… what have you been thinking in that big head of yours, Ash Ketchum?" She patted his head as Ash gave her a small smile. He took in another cool breath of air, to slow down his heartbeat. He had finally made a decision.

"Well, I can't tell you right now…

But I will in a year from now."

May huffed and looked at him, deflated.

 _A year?_

 _Year?!_

Was she able to wait that long?

"Hey, it's not nice to keep secrets from a best-friend, especially ones you've saved the world with."

Ash grinned, knowing he pulled on her nerve. "Sorry! But I promise… one year from now."

May was slightly disappointed, one year was a long ways away. What exactly would he need to do for one year? What did he need to discover? But she decided, Ash was worth waiting for.

"Swear on it. Cross your heart."

The trainer made an X shape over his heart.

"I swear. And when I come back, I'll make up for being busy, May." Ash gave her a smile that made May's heart instantly skip a beat.

* * *

 ** _Alola Harbour._**

 ** _Present._**

 ** _9AM._**

The Raven haired trainer had just arrived at the Alolan dock, grabbing his backpack and making sure Pikachu had a place to perch on his shoulder.

"It's time buddy. Are you excited?" Pikachu nodded enthusiastically. Pikachu loved to see old friends almost as much as Ash. Ash smiled to himself at his partner's excitement. He took a deep breath, taking in the incredible sight of the region. He grinned as he heard the steel drums, instantly making him even more ecstatic.

"It's been a while, Alola…. Let's go!" He raced off the dock after showing his ticket to a very confused and concerned ticket attendant.

"Sir, be careful, the docks are slippery!" The attendant yelled. Ash however, let the warning flow out from one ear to the other as he raced towards the Pokémon school. As he turned the corner to face the school, he suddenly stopped as his heart fluttered.

May.

May was inside.

She was here. Less than ten feet away.

The trainer looked over at Pikachu, who nudged him to go forward. Ash gave Pikachu a small smile and walked inside slowly. As he opened the door, the sounds of excited young trainers filled his ears. But the only voice he was looking for reached out to him….

Her distinct voice ringed out in the crowd…

…

"THAT'S MINE!"

"No it's not May! Mom gave it to me as a snack!" The younger Maple exclaimed as he tried to stuff the giant cookie back into his backpack, silently wishing he never opened his backpack in front of his cookie monster of a sister.

May pouted, "You don't love me, do you. You just want me to starve."

She patted her lean stomach, which – on cue, started rumbling. However, it wasn't just one stomach rumbling, another stomach rumbled right behind her.

Her eyes widened as she realized that only one other person's stomach could rumble that loud…

"Ash!" She exclaimed, as she turned around and came face to face with the teen's brown eyes.

He shot back a grin and patted his stomach.

"Glad to know I'm not the only person that's hungry." He chuckled, as Max's eyes lit up and he gasped.

"It's really you, Ash!" The boy hugged the older trainer in glee.

"Hey Max! How ya doing?" Ash smiled back at the navy haired boy. "I think you're even taller than me when I was ten."

Max grinned at the raven-haired trainer as he let go and fixed his glasses.

"Yeah, I get that a lot." Max laughed, then continued on for a moment to tell Ash about how he got recommended to study at the Alola school.

 _Thump thump._

 _Thump thump._

May could almost hear her heart jump out of her chest as she stared at Ash, totally not expecting him to be here so early.

She suddenly felt self-conscious.

Sure, her hair and outfit were fine, she looked presentable enough, she supposed, but she was still nervous as hell, cursing the butterflies in her stomach. She never felt like this before... not recently anyway.

May looked over at Ash, who had also gotten considerably taller, and slightly more filled out body-wise. But his face still had that go-lucky excitement on it, something that she would never get tired of seeing. It was infectious.

"Earth. To. May." A hand waved in front of her dazed face, she followed the hand to the person it belonged to.

Ash.

"Oh, I was just so hungry…" She darted her eyes around to look for an excuse, then eyed Max's backpack. "Which I wouldn't have been if Max would share his cookie!"

Ash chuckled to himself. _Same old, same old_.

"Glad to see you guys haven't changed at all. Where's your trusty restaurant guide May?" He probed.

"Oh right!" She reached into her fanny pack and pulled out a brochure.

"How are you guys feeling about fish and chips? They also make this amazing dish called Malasadas… We have to try them!" She stared at the brochure with a twinkle in her eye, her mouth already watering with anticipation.

"Aw man… You guys are going to love them. They come in so many flavours!" Ash said excitedly.

"Alright, then follow me guys!" May began walking out of the building, signalling the group to follow her lead. However, just at that moment, loud speakers signalled an announcement.

"Alola! All student's, please report to gymnasium A to continue registration. I repeat, all students, please proceed to gymnasium A. Thank you!" The intercom ended, and Max looked at May, who frowned.

"Aw Max… if you want, we can wait until you're done your registration, it probably won't take that long, right…?" May asked, though secretly she just wanted to make a straight beeline towards the restaurant. Her stomach could only take so much hunger. And Max knew that as well.

"No guys, you both turn into angry Mankey when you don't get any food, just make sure you bring me leftovers!" Max squinted his eyes at May.

"Heh, alright then, just message me if you need anything. Ash, let's go!" She grabbed the trainer's wrist without thinking and dragged him towards the restaurant. Max smiled at them both and headed towards the gymnasium.

* * *

"Mmmm….. can you smell that?" May sniffed the air, taking in all the various smells of sweet potatoes, aromatic fish, and the famous fried pastry donut.

"It smells delicious….." Ash spoke dazily, food was an intoxication for him too. He straightened up and glanced down at their menus.

"Ready to order, May?" Ash asked.

"Yup, I'll have the fish and chips deluxe, with coleslaw salad, and one regular malasada, one chocolate one. Think you can remember that?" She inquired as Ash made a mental note.

"Yup! I got it. Be right back!" He stepped out of the table and made his way to the cashier to order, May took this opportunity to take out her phone and check up on Max.

 _'No new messages.'_

She smiled to herself. _Max is probably having too much fun…_

May started going through her cellular device, and clicked on the photo application. The coordinator loved taking pictures of food and other delicacies, so she wanted to show Ash a picture of her latest culinary adventure – caviar, basically fish eggs. She laughed to herself thinking of how disgusted Ash would be when she told him what it was.

As she continued flipping through her old photos, she caught a glimpse of a photo that she didn't particularly enjoy looking at. In it, Drew held the Ribbon Cup proudly, and she stood beside him with Blaziken, along with two other coordinators, a red-head named Solidad and a purple-haired eccentric man named Harley. You could almost feel the disdain and hatred radiate off the screen from the purple coordinator. She looked at herself in the photograph and paused, disappointment and regret slowly creeping up on May's mind again.

"Penny for your thoughts?" The black-haired trainer appeared, with a tray of scrumptious food. May looked up, surprised at how swiftly he'd come back. What she heard was true, Alolan service was impeccable, efficient and friendly.

"Oh wow, that was quick!" She quickly moved her glass to the side make way for the trays. Once Ash was seated, she looked at him.

"I'll tell you... AFTER I eat all of this amazing food!" The coordinator picked up her utensils, and Ash did the same.

"I agree, I can't keep a conversation up while all of _this_ is in front of me."

They both grinned widely and nodded, digging into the food. They earned a few looks from the neighboring couple who were in awe at how much they were eating. Around ten minutes later… they had finished all of their meal. Ash covered his mouth and burped, and May did the same.

"Excuse me!" They said in unison, then paused and laughed.

"You finally learned your manners?" May grinned back at him, remembering all the times he used to burp freely without any regard of who was around.

"Hehe… Yeah, I realized how gross other people found it when Snorlax burped in my face after eating." He grinned back, then slowly changed his expression into more of a concerned one as he remembered May's face before they started eating.

"So what was that all about? You were staring at your phone like you were sad about something. Is everything okay?" Ash asked.

May fiddled with her phone uncomfortably. She didn't want Ash to know she failed again. She was afraid…

Afraid of letting her first mentor, down.

Afraid of letting the person who always cheered her on, down.

Afraid of seeing the disappointment on yet another person's face.

Afraid of re-living the regret, one more time.

Ash could sense it was something she didn't want to talk about, and that had him worried. He didn't want her to suffer alone, he had to say something…

"May, you know you can tell me anything, right?" He bit his lip a bit then ran his fingers through his hair nervously. He had to tell the brunette something difficult too.

"If it makes it easier, do you want me to talk about my problems first?" He nudged her. She nodded slightly in agreement.

"That would make it easier." She said, releasing the breath she didn't know she was holding in.

Ash shut his eyes then opened them again, to look straight into May's eyes.

"May... I lost again. It was hard, but I decided to try my old way one more time last year to see if anything would change. And it didn't."

He said hardly, darting away from her eyes. He was ashamed and angry at himself, but he wouldn't beat himself up for it anymore. May's eyes softened as she gave him a small smile. Here Ash was, not afraid of admitting his short-comings to her, she decided to be vulnerable with him as well.

"Ash… I lost too."

Ash tilted his head and stared back at the brunette, choosing his next words carefully. He didn't want her to feel worse than she already did.

"I heard, I was going to ask you about that, but I didn't want to force you May."

May blinked back at the trainer.

"How did you know, Ash?"

"Well, you didn't think that I'd miss your grand festival performance, did you? I watched you on TV as much as I could. Well, like a couple of minutes of it."

Suddenly, a flying malasada hit his face, leaving chocolate all over his face.

"Ash, why didn't you call me instead?! Or I don't know… text me." The coordinator looked at the trainer, who licked the icing off his cheek.

"May… I don't have a phone! And by the time I saw you on screen, you were already on the field May… I only caught the last moment. Even if I called you using the Pokemon Center's phones, you wouldn't be able to pick up! Thanks for the chocolate by the way."

He wiped off the chocolate on his cheek with his finger then licked his finger. May scowled at him for a moment, until she broke out into a smile.

"Excuses, always excuses with you. Do you need me to buy you a phone, Ash Ketchum?"

Ash grinned at her.

"Nah, I find phones distracting… Maybe later."

"Alright , flip phones aren't distracting, all you can do is call or text people, and play snake. And you can even mute it if it's bothering you! Magic." May shot him a triumphant smile back.

"You know, I didn't really think about a flip phone. Good idea May!"

May shook her head at the trainer while smiling. Just a minute ago she was struggling with her inner demons, yet Ash was able to make her forget them so easily. He hadn't changed at all since last year.

"Anyway Ash, it's been a year. I think it's time you told me what you've been doing."

Ash cleared his throat and picked up the glass of water, taking a sip. He set it down gently then locked eyes with May's.

"Well, a lot."

May adjusted her seat to prepare herself for what Ash was going to say next.

"Mhhm. You've been gone a year, and you promised that you'd tell me what your plan was when you came back, so please explain."

He nodded and let out a short sigh.

"Well, I was getting tired May. Tired of losing. Tiring of putting in so much work to not get that title I've been working for. I know that each time I went on a new journey, I was learning something new, I learned new skills, met new Pokemon. I'm not taking that for granted, I've enjoyed every bit of it. But it's time for a change. This time it's going to be different. This time, I'll use my old Pokemon I'm familiar with, I'll help them grow even stronger and learn new techniques for them. This time, I'll travel with friends who have supported me since day one. Because when you have to adjust yourself, it can slow your progress. And that's something that every single veteran trainer I've met has taught me."

May nodded at the trainer. She could feel his passion embedded in his speech. And his disappointment at not being able to grasp victory. It was a feeling that unfortunately, she knew all too well.

"I'm sorry you weren't able to do as well as you wanted to either Ash. It hurts when you're inches away from victory, but you're not able to get it…. I know that feeling. What exactly are you suggesting we do?"

Ash suddenly took the brunette's hand in excitement. May blinked back at the trainer, taken aback by his behaviour.

"Travel with me again, May."

May could feel the heat rise to her cheeks, Ash wanted to travel again, with her? She couldn't tell if this was real, or if she had just imagining everything that had transpired a moment ago.

"I-I would love to Ash. But are you sure about this?"

Ash nodded eagerly, then let go of her hands to take out some things from his backpack. He unzipped the sack and pulled out a brochure of a new region, along with some old trinkets.

"Look, the Medola region. They have contests, a league, perfect for us. Misty, Serena, Max, Dawn… Brock, we can all go together!"

May smiled back at him. Her stomach was tingling in excitement just imagining travelling to a new region with all of their old friends. But soon, her smile turned into a frown.

"What's wrong? You don't like the idea?"

"I-I do Ash… it's just that, I'm not sure if I'll be able to travel with rivals again. Granted, Dawn and Serena aren't as condescending as Drew and Harley, but I can't help but start comparing myself."

Ash looked at his brunette friend sadly. She was always so confident, but losing the recent Grand Festival had taken a toll on her. He wanted her to go back to being the old May he left in the Battle Frontier. Strong. Hopeful. Never backing down from a fight even if the odds were stacked against her… he saw so much potential in her, if only she could see it in herself.

"Well, I haven't mentioned it to the others yet…We could always make the squad smaller…. But May, comparing yourself to others is perfectly normal, just don't do it negatively and please don't beat yourself up over it. And if you ever feel down, I'll be here to pick you up. I promise. You know I always keep my promises. Even if I'm late in delivering them."

He grinned at the girl sitting in front of him. She couldn't help but return the grin back at him.

"I hate you, Ash Ketchum."

Ash immediately fake frowned.

"What did I do?"

May smiled as she picked up another fried malasada.

"You made me believe in myself again. And I can't believe I said something as cliché as that."

 _CHUCK!_

The fried pasty made contact on Ash's face, this time instead with powdered sugar spread all over his face like fresh snow.

"Hey, I'll eat these all day if you feel better!"

May laughed as she got up, heading to the door while smiling to herself.

"I'll be glad to go travelling with you again, Ash. And bring whoever you want to, I don't mind."

Ash nodded, and got up after brushing the powder off his face. He still looked like a circus performer, but he didn't care. He ran behind May until he caught up to her, Pikachu running behind them as well until the mouse Pokemon jumped and perched on Ash's shoulder.

The pair were more content in this moment than they had ever been in the past year. May stole a look at Ash, who was opening the brochure to the Medola region to talk about how great it would be. He really was child-like in a way, infectious curiosity filled his face as he started telling May about all of his new Pokemon.

The brunette couldn't help but notice that one thing had changed in Ash.

He was much more calm in certain manners, it's like he was both at peace with his fate, yet always challenging it at the same time.

The pair walked back to the Pokémon school to meet Max, who was spamming May with texts about being a bad sister, as part of the sibling blackmail they regularly did to themselves. Ash laughed as he went through all the old texts with May, not surprised that Max was that cunning.

As the pair walked through the busy Alolan streets, a cool breeze flew through the coordinator's brown locks. She shut her eyes as she enjoyed the delightful breeze, feeling truly hopeful.

She knew, that the next year would hold many new memories.

And she looked forward to spending them all with Ash.


End file.
